Hydrochloric Acid → Ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1752644Notes

Reaction equation

O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12.N1C=CC=CC=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Na+].[I-:40].Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[I:40][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12

Participants

Conditions

Temperature: 70 °C

Procedure

A 0° C. solution of ethyl 4-hydroxy-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (10.0 g, 42.7 mmol) in acetonitrile (200 mL) and pyridine (4.13 mL, 51.2 mmol) was treated dropwise with Tf2O (8.65 mL, 51.2 mmol). After 1 h, the reaction mixture was treated with NaI (19.20 g, 128 mmol) followed by dropwise addition of 3M HCl (17.08 mL, 51.2 mmol) and warmed to 70° C. After 3 h, the reaction mixture was cooled to ambient temperature and added to a sat. aq. solution of Na2S2O3. After stirring for 15 min, ethyl acetate was added and the layers partitioned. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (14.7 g).

Workup

waitAfter 3 h
temperaturethe reaction mixture was cooled to ambient temperature
customthe layers partitioned
washThe organic layer was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e24b3608d123461080f3bb1f709871d2
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163023B2

Reaction notes

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